Last year, I decided to see Lake Michigan from new angles. It is the centerpiece of the Upper Midwest, but I’ve always thought of it as an ocean surrogate because I’m a New Englander at heart: When I see water all the way to the horizon, I instinctively think of the vast churning Atlantic Ocean and remember growing up a few miles from Cape Cod Bay.
So I hatched a plan to circumnavigate the lake’s southern reaches on bike, with a big assist from my father and the cross-lake ferry that leaves daily from Milwaukee during warmer months. We’d make a lake loop over a long Labor Day weekend: ride the commuter rail up to Kenosha, Wisconsin, bike north from there to Milwaukee, and then pedal south from Muskegon through Michigan and Indiana and back home. Four days and 350 total miles, 227 by bike and 79 by ferry.
At least that was the plan. As I and my father—who gamely flew from Boston to join the adventure—quickly found out, the best-laid plans often go astray. Thankfully, though, serendipity can transform a challenge into unexpected pleasures. In our case, serendipity also saved us from my own ambition.
Chicagoland’s sprawl is massive but no match for the commuter rail train that carried us quickly through North Shore suburbs and into Wisconsin on the last day of August. We embarked from Metra’s terminus in Kenosha, our bicycles laden with panniers full of high-energy snacks, water and maps, in case of iPhone failure.
By 9 a.m. we were on the Kenosha County Bike Trail, a nearly 20-mile path heading north toward Racine. Like all rail-to-trail conversions, which reinvigorate fallow land for public use, it was flat and easygoing, giving us plenty of time to acquaint ourselves with the backyards and pre-harvest fields full of food that slipped past as the sun rose.
We snaked through post-industrial Racine’s sleepy neighborhoods, detoured around closed trail sections, and carefully negotiated dusty orange-coned construction zones. After missing a turn in Oak Creek, Wisconsin, and finding ourselves in territory loathed by cyclists the world over—a busy four-lane road with small shoulders—there was a sudden somber moment. I noticed a roadside memorial, and looked up to see the Sikh gurdawa where a crazed white supremacist had killed six people less than one month earlier.
I didn’t expect this inland part of the trip to be particularly stunning, and it wasn’t. When the lake appeared through the trees of Grant Park in South Milwaukee, we coasted downhill to a beach and I ecstatically jumped in. After riding through the thickly forested park along a high bluff dramatically framing the lake—the highlight of the day for me, by far—we reached our destination: Sheridan House, a “Boutique Hotel & American Bistro” in Cudahy, a leafy lakeside town just south of Milwaukee’s port.
It was the closest lodging to the most crucial part of our plan: the Lake Express ferry leaving early the next morning. After dinner and a few soothing local Lakefront Brewery beers we collapsed into sleep, oblivious to the wrench about to be thrown our way.
Improvising an exit plan
Lake Express advertises its high-speed ferry as a “fun, fast, and easy transportation solution.” But when we arrived at the checkout counter at 5:15 a.m. and learned the ferry had just been canceled indefinitely due to an engine failure, “nonexistent” seemed a more apt descriptor. As a gorgeous salmon-orange sunrise lit up the lake, we sat fuming, staring at the ferry that refused to cooperate with our well-crafted plan.
Our plan, which had seemed so solid the day before, was on the verge of collapsing after we had biked only 35 miles and barely seen the lake. After a flurry of morning phone calls, a possible solution emerged. If the ferry was resurrected in time for the next morning’s 6 a.m. departure, we could rendezvous in St. Joseph with some friends on Labor Day as they drove south from a weekend in Leland, Michigan, near Traverse City. It was a long shot, but the only option other than turning back to Chicago in bitter defeat. We booked another night at the excellent Sheridan House and hoped Lake Express’ mechanics were talented.
As it turned out, our second day in Milwaukee was full of memorable serendipitous moments showcasing some of the Midwest’s best qualities. Milwaukee and its environs, thankfully, abound with well-marked bike routes. We pedaled past the city’s landmark winged Art Museum as the city woke up, pausing for an outdoor breakfast at an Alterra’s coffee shop in Veterans Park.
My father, whose longest stay in the Midwest was for boot camp at Naval Station Great Lakes 45 years ago, was struck by the hospitality extended to us throughout the weekend. “Someone always seemed to be there to direct us to a trail or street when our maps failed us,” he remembers.
After lunch at a vibrant farmers’ market, a cyclist approached us as we studied a map. Soon he was leading us to what he said was an overlooked local gem at the end of a grand driveway: the Archdiocese of Milwaukee’s gothic headquarters, surrounded by rare old growth forest.
We bid him farewell and ventured into the cool ancient woods. A few hundred yards along a footpath, a small cemetery appeared in a clearing, the final resting place of hundreds of nuns and priests who had given their lives to the church. The oldest 19th-century tombstones offered German names, a reminder of Milwaukee’s earliest history. Quieted by the utter silence of the scene, we slowly emerged from the forest, ready for the adventure’s next chapter, wherever it might unfold.
Welcome to cycling paradise
A phone call woke us up at 4:30 a.m. the next morning: the ferry was back in action and would leave at 6 a.m. All was not lost, and soon Milwaukee’s skyline was receding into the horizon.
The 200-foot-long catamaran cruised at about 25 m.p.h., which doesn’t seem fast until you walk onto the vessel’s roof deck and nearly fall over due to intense gusts and 3-5 foot swells. Then the motion sickness warning issued by the captain during departure makes sense. As I slowly made my way back to the cabin, with nothing but water in all directions, it was abundantly clear that Lake Michigan is more inland sea than lake.
As we approached the shore, we entered cycling paradise. We never really left it during the next two days as we made our way south about 100 miles through Grand Haven, Holland and South Haven. During one stop, my father explained the main reason he loves to bike. There's a certain Zen state that I sometimes reach,” he said. “The changing terrain and multi-sensory experiences occupy just enough of my mind that I don’t think about anything else, which is very relaxing.”
Despite extreme heat and a few major hills, we both found it easy to reach that Zen state of relaxed concentration on the way to St. Joseph. (A mandatory stop at New Holland Brewery may have helped a bit; bicycles and craft beer go hand in hand.) Just as important, we stayed on pace for our mid-afternoon Labor Day rendezvous, making sure not to linger long near South Haven harbor’s lighthouse, which reminded me of Cape Cod.
As with any good bike trip, what remains in mind months later are the unexpected encounters: an Amish couple visiting South Haven surprisingly curious about our outfitted bikes and destination. A massive coal plant appearing suddenly around a bend, and the half-mile-long freight trains feeding it. A child playing outside at dusk cheering us on.
A final moment of almost absurd friendliness marked our finish line in a St. Joseph park overlooking the lake. After getting off our bikes, a woman excitedly asked where we’d come from. We recounted the trip, and she was so excited that she asked her husband to take her picture with us. Exhausted and sweaty, we obliged, and I couldn’t resist feeling a small pang of pride. Against all odds, we had somehow found a lucky ride home, which miraculously appeared an hour later. (We also found a place to stow our bikes for pick-up later on—thanks to Boulevard Inn and Bistro.)
No, all did not go according to the original plan. But by the end of day three, as we collapsed in a Saugatuck motel after riding 50 miles in grueling heat, we both knew that was for the best. To have completed the original route would have been more work than fun, allowing no time to stop and appreciate the lake—which was, of course, the whole point. Sometimes things have to go awry to fall into place.